A Match Made in Hell
by Klarobass
Summary: After Chuck and Blair witness an argument between Jack and Georgina, they realize Jack and Georgina have feelings for each other, but refuse to admit it. They decide to get them together. Will their scheme succeed or is it doomed to fail? Three-shot Rated M C/B J/G
1. The Argument

_**Disclaimer: I don't own Gossip Girl or its characters. All copyrights belong to their respective owners. If I did, season 5 wouldn't have happened.**_

 _ **Special thanks to Chairship, liarspromise and Scarlett2u and their editorial eye.**_

Exasperated, Blair strode into the Bass townhouse. She had a long and tiring day at Waldorf Designs, finalizing the latest designs for the launch of next season's Fall line. She just wanted to relax and settle herself in her husband's comforting arms.

It had been several excruciating hours since she had last been in her husband's embrace. Chuck always knew how to calm her scattering worries and thoughts. They were married six months today, and all she wanted was for her husband to reassure her that everything would be okay as he made love to her, showing her that she was the most beautiful woman in the world.

She sighed contentedly as she realized she never wanted to lose what she had with Chuck. She never understood how she resisted him for so long, only to finally admit what she knew her heart truly sought. She swallowed, letting her troublesome thoughts wash away from her flooded mind.

As she walked into Chuck's office, taking in his form, she noticed how dazzling he looked in that suit. She just wanted to rip it off him and show him how much she loved him. But when she looked up at him, all she saw was his worried face. "Chuck," she said soothingly, "is everything alright?"

He tore his gaze away from the papers he was peering through, to gaze into his wife's concerned, deep chocolate eyes. He knew she was worried. "Just work stuff," he responded half-heartedly. "Nothing to worry about. Besides, I'd much rather talk about your day, my breathtaking wife."

Chuck's comment caused her to flush crimson. He always knew what to say to make her feel like she was the most beautiful woman in the world. God, she loved this man. She studied his eyes carefully. "But something is up, and I want you to know you can talk to me, Chuck. I'm your wife and I will support you through everything."

"It's the board," he revealed in an almost silent whisper. "They still think I killed my father. How long before they decide I'm not worthy enough to run Bass Industries?"

Blair felt her veins turn to ice. How could they believe Chuck, the man who had run their company over four years do such a thing? How could they not see what a wonderful, intelligent, charming and innovative man he was? Chuck helped rebuild the company after Bart's "first" demise, doubling its profits and then some, and _now_ they doubted him?

Their loyalty to the great Bart Bass caused her heart to ache for her husband. Bart was one cold bastard, and they didn't even see it. Sometimes she swore that there wasn't a heart beating in Bart's chest. Bart didn't know what love was, so it was no wonder Chuck always doubted his wealth when it came to love. Bart had made him feel like nothing he ever did would be good enough.

She wished even after six months that man wouldn't have such a forceful grip on Chuck's fragile heart. She understood it though. He didn't even have to tell her. It was an unspoken feeling that even after all Bart did, he was still Chuck's father, and nothing could ever change that. Even after everything, Chuck still craved Bart's love and approval like a child craved candy.

"What's worse is they think I married you to avoid suspicion of the murder, and prison," Chuck frowned. He never wanted Blair to think he married her out of fear or convenience. He married her for love and he hoped she knew that with every fibre of her being.

"How could they think such a thing?" she said, peering into Chuck's blazing gaze. "Chuck, I married you because I love you. You married me out of your love for me, and if they can't see that, they're idiots." She leaped into his embrace, wrapping her hands around his neck. "I love you so much, Chuck, and I can't stand to see this man hurt you so much. You've become a man in a way your father never will be."

He beamed at her words. He loved her for the way she was there for him, even if he sometimes didn't know if he really deserved her. But he knew that she loved him and would stand by him. "Jack is helping me gain support within the board," he revealed. "Now," he said, his hands caressing her arms. "Enough about me. Let's talk about you. How's the life of the most amazing CEO?" he asked with a satisfied smile.

Blair looked down, making sure to keep her perfectly still composure. Her breath came to a halt as she let Chuck's question ring in her ears. His resolute faith in her astonished her. Even after all the years of insecurities, scheming, and manipulation he still had complete trust in her. It was an incredible feeling. Even after all their heartbreak, misunderstandings, and imperfect reunions in the past, the fact that he still had this much conviction in her made her heart jump out of her chest with joy.

After the whole Prince Louis ordeal and her brief dalliance with Humphrey, she, at times still doubted whether she deserved a love so deep. But here they were, happily married, and as much in love with each other as they always had been. She knew she wasn't going to do anything to mess this up.

She looked into her husband's heated gaze. It was a look of passion, desire, and love, and still couldn't believe she was married to Chuck, the love of her life. Someone who never thought he deserved love. But he did, and she would spend the rest of her life showing him that. "It could have gone better," she murmured. "My mother wants me to hire Jenny Humphrey as the head designer, and for me to handle the more administrative responsibilities," she said through clenched teeth. "As if I would ever hire that social climbing wannabe after what she did to us."

Chuck sighed deeply, making sure to be careful of the words he chose next; he never wanted to lose Blair again. "Blair," he said softly, warmly, as he traced his fingers down the small of her back. "Jenny's been back two months now, and she's tried to fix things with you. It's been four years since our deception," he started, causing Blair to flinch at the word 'our' next to Jenny's name. "You forgave me after everything. Don't you think it's time you do the same with her, even if it's only so that we can move forward. What happened that night is my biggest regret, but if we're to move forward, maybe it's time to let go of the past completely."

Blair relaxed into Chuck's gaze, kissing him softly on the lips. "You're right," she admitted. "It's just every time I see her; I think of how she almost destroyed us."

"But she didn't," he told her, kissing her knuckles affectionately. "Because our love is inevitable. But if we are to move on with our life, that means forgiving Jenny. If we allow ourselves to hold onto the past, can we really move forward?" The way that Chuck looked into Blair's doe eyes made her heart melt. He was looking at her with such love and adoration.

"Besides," he said, touching her lips with his own. "She has a great fashion sense. And if we're being completely honest, you always were a natural born leader. You were meant to lead, not follow. You love to give orders, and this allows you to take a more direct role in managing your company. Running the operations yourself. And not to mention, you would get to finalize everything Jenny designs."

She beamed at the way he brought such tranquility to her troubled mind. He always knew what to do and say to her.

Right now she felt desire burning in her. She didn't want to think about Bass Industries, or Waldorf Designs or Jenny fucking Humphrey. She wanted Chuck inside her. "Chuck?"

"Hmm."

"Let's not talk anymore," she said lustfully. "What do you say we take this to the bedroom?" her eyes darkened seductively as she felt her desire soak down to her groin.

"I guess there could be some pleasure in that," he smirked, capturing her lips with his own as his tongue danced with hers in perfect rhythm.

Their tongues began to battle for supremacy, as they began to thrust against each other. Before she knew it, Blair removed Chuck's jacket and shirt, as Chuck ripped off her dress revealing the black lace lingerie. His hand traveled down her body, moving into the black lace, and into her core, causing her to groan "Chuckkk." She purred at the way he was causing her body to squirm with desire.

"You're so wet, Blair," he whispered lustfully.

"Blair's hand reached into his pants and through his boxers, stroking his already hard cock. "And you're so hard," she responded.

"Only for you," he began to sweep his tongue into her mouth once again, heightening her arousal even further. He unclasped her bra, exposing her breasts to him. He swept his tongue over a taut nipple, drawing it into his eager mouth and sucking hard. He began to palm her other breast while his tongue laved into the taste of her other one. "Chuckkkkkk," she cried in pleasure.

God, she didn't not want him to stop. She was so turned on right now, but knew the best was yet to come. He began to move his talented tongue over to her other hard nub, whirling his tongue over the rosy bud. Her cries of pleasure only increased further.

Blair removed Chuck from his pants and boxers, freeing his iron cock which was more than ready for her. She took her hand, and starting at the base of his penis, began to move her hand up to its head, eliciting a blissful groan from Chuck.

Chuck's hand snaked lower as he began to knead the curve of her ass. He then yanked down her panties in one swift move, and took her to the bed, laying her on her back. "Blair," he purred. "You're so beautiful," he groaned in his aroused state, yet he meant every single word.

There wasn't a woman more beautiful to him

He took two fingers and slipped into her core, causing Blair's hips to buckle and writhe as she tightened around his dexterous fingers. He pulled out as his tongue began to sweep onto her clit, causing Blair to squirm at what that sinful, and skilled tongue was doing to her. She couldn't handle it anymore, she needed him inside her. Now.

"Chuckkk," she cried blissfully again. "I want you…inside me," she said with trembling breaths as his tongue continued its assault on her.

With her latest request, he went to their nightstand, grabbing a condom, and rolling it over his strained cock. With one swift movement, he spread her legs apart to gain further access and he entered her gently. He then slid in deeper and began thrusting into her.

She felt herself tighten convulsively around his cock. Her breath began to speed up as she began to pant his name over and over as he rocked into her again and again, causing an orgasm to explode through her. They both came together, as he erupted into her, completely filling her.

They held each other close as their breathing slowed back down to normal. "I don't think this feeling will ever go away," she sighed happily as she rested her head against his chest, listening to his heartbeat.

"Which feeling is that?"

"The feeling of complete bliss after we've made love," she admitted. "I love you, Chuck, and that's never going to change. It's only grown stronger.

"I feel the same, Bass," he said, causing Blair's heart to melt over the way Chuck referred to her as 'Bass'. Blair didn't think she could tire of the way he looked at her when he called her that. It made her heart soar knowing that the moniker was their little secret, something he called her only when they were alone because no one could understand what it truly meant to them.

Blair had grown up with her Waldorf identity, and even though legally she was now a Bass, professionally she decided to keep her Waldorf name. It was a part of who she was, and her success derived from being a Waldorf. "Promise me something, Bass," she said, looking into his blazing eyes.

"Hmm."

"Promise me we'll never lose this," said Blair with complete gratification. "This feeling. The way you look at me with such love, like you worship me."

"Blair, that could never change. Haven't you figured it out yet?" he said, kissing her tenderly on the lips. "You're it for me. It's only you."

She beamed at him before heading off to start the water for their shower.

Later, as they got dressed for their dinner out, they heard angry voices coming from downstairs….

Jack and Georgina?

Blair looked at Chuck in surprise.

"He's supposed to drop off papers for me to review before a big meeting first thing tomorrow," her husband whispered.

They headed stealthily down the stairs to the dining room to overhear what sounded like an argument brewing between Jack and Georgina.

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Tension was radiating from the room. It left an unsettled feeling in Blair's stomach as she tried not to be seen from the living room. They needed to know what was going on, and what better way than to listen to those ringing voices echoing down the hall?

Chuck and Blair snuck themselves into the dining room, located to the left of the living room. It also made it easier to understand what Jack and Georgina were saying.

Jack and Georgina were so busy arguing that they didn't even notice Blair and Chuck sneak past them.

"I am not your fucking lap dog, Sparks," Jack hissed angrily, his voice cracking with every word he spoke. "I will not be used as your scheming weapon or some plaything that you can fuck whenever it pleases you, only to be tossed aside when you get bored. I'm not Philip!"

Blair tried to register Jack's words.

Jack and Georgina? Georgina and Jack? No, it couldn't be. Could it? Jack and Georgina were too crazy to find happiness, weren't they? But then again, they were a match made in hell - a perfect match, really. But could they ever admit that there was something blossoming between them?

Georgina had divorced Philip only two months ago. He was too amiable for Georgina's liking, always taking orders at her whim as if on a leash. She wanted a man who would challenge her. Blair could understand and appreciate that. Philip had never challenged Georgina. He was nothing more than a trophy husband.

Blair had a feeling Georgina wanted someone who made her feel alive and made her skin burn with desire.

It was obvious from the heated discussion that Jack and Georgina were having sex, but why was Jack so angry about it? She could feel the heat of his eyes as they sizzled angrily into Georgina's sea blue eyes.

"Jack," Georgina spoke irritably, her fingers tracing patterns over her tousled hair. "We both knew it was a one-time thing, and you told me you were fine with it. Besides, I know you; you're Jack Bass," she said as if that was all the explanation in the world.

Blair's face formed a scowl as she looked into Chuck's hazel eyes. She recalled a similar instance where she had said those same words to Chuck, when they had played that game. As it turned out, Chuck hadn't done what she thought he had, he'd just had a headache. Needless to say, they spent the remainder of the night roleplaying and making love to each other.

Blair recalled how simple things had been back then. Before everything had fallen apart, before all the wrong timings, princes, and Dan Humphreys. A time when it was just the two of them, irrevocably in love and just trying to make one another happy.

The course of true love had never been simple between them, but in their honeymoon phase, in that moment, it was perfect. A time before Elizabeth and Jack, before everything plummeted downwards.

She gazed into her husband's eyes with an unspoken question. Asking if he saw what she did between Jack and Georgina.

"Meaning?" Jack asked, his mouth twisting into a scowl.

"Meaning?" Georgina repeated mockingly. "Meaning you don't want a relationship, Jack. I know you. You make your nephew look like Prince Charming."

Jack blanched at Georgina's harsh words, completely aware of what she was telling him. She was talking about his womanizing past, much like his nephew had.

Had. As in the past.

Why couldn't she see that was all in the past? That he could change? If Chuck could change and settle down with the woman he loved, why couldn't he do the same?

Was he just a fuck buddy to Georgina? The thought was unsettling in Jack's mind, as the anger from her harsh outburst rippled through him in a heated frenzy. "You know, it's no wonder you divorced Philip," he spat without thinking how harsh he sounded. He was so livid about how quick Georgina was to dismiss him that he didn't think. "You can't stay interested for more than a day," he crossed his arms over his chest. "Face it, you didn't love Philip. He was nothing more than a pawn in your arsenal, and maybe the thought of something real with me terrifies you. Come find me when you're ready to stop running away," he said before storming away.

The two of them left the Bass townhouse in a fury, going in opposite directions as if the other was the plague.

Blair and Chuck had managed to stay hidden, without being seen or heard by Jack and Georgina. The silence in the room was deafening, and she had to think, what should they do?

Should they help them get together?

Jack had hurt Chuck and her in so many ways, it was overwhelming. And Georgina had been a constant pain in her ass throughout her high school years, college years and beyond. Yet Blair couldn't help but wonder if she owed them this.

Georgina had helped her escape the rooftop after Bart's untimely demise. If it wasn't for her, Blair wasn't sure she and Chuck would've been able to leave unseen, and Chuck might've had to go to prison. The thought sent a chill up her spine as her mind began to recollect that night. The way Bart attempted to murder the love of her life, his son, her Chuck.

A life without Chuck was a chilling thought. He held her together when she doubted herself and she did the same for Chuck. They were inseparable. They were two damaged people who loved each other with every piece of their beating hearts and completed each other. Without the other, their hearts would become hollow. She never wanted to lose Chuck again.

Perhaps they owed some of their current happiness to Jack and Georgina. Jack helped them procure their wedding license, without any suspicion from the authorities, While Georgina helped them plan their escape without any suspicion from the feds, and helped Jack organize their wedding and bring the guests to the wedding, the happiest and scariest day of Blair's life.

Scary, because the thought of Chuck going to prison over his father's death - a father who didn't show any semblance of emotion towards his own flesh and blood - shook her to the core. It was a feeling she couldn't seem to let fade from her mind.

A father was supposed to protect his child, not hurt him. She knew one day she wanted to have children with Chuck, and she could see them having a son. She couldn't see Chuck being so cold and cruel towards their child. In fact, she knew Chuck would be a loving father who would show their child that he was loved with all their heart.

So they owed Jack and Georgina, but could she forget the pain they caused them? She knew Chuck forgave Jack for everything, but could she forgive him too?

Jack and Georgina were so ruthless and cunning, they made them look like Santa Claus and the Easter Bunny by comparison. Chuck and Blair schemed to protect those they loved, but Jack and Georgina schemed in the past to destroy people, including those Blair cared about. Including the man she loved, her husband.

Could she just forget that?

Blair decided to broach the subject with Chuck, her partner in crime. Together, they would come up with a plan.

She wondered what Jack and Georgina would be like as a couple. Could Jack actually be happy? She couldn't remember a time she saw Jack happy. He always seemed so hell-bent on revenge and hatred, it was hard to imagine Jack being happy after all that.

But she had also seen how broken Jack seemed at Georgina's reaction. Was he already developing feelings for her?

They entered their bedroom as Blair wrapped her arms around her husband's waist, and kissed him ardently. He returned the kiss with just as much passion. She let herself melt into the kiss for a few beating seconds before she reluctantly pulled away. "So…" she cooed, "Jack and Georgina? Georgina and Jack?"

Chuck's eyes reached Blair's and he beamed at how happy she looked, at how happy they were now, and it made his heart swell with joy. Especially given that he was a big contributor to her happiness. He chuckled at the way Blair phrased the question about his uncle and whatever Georgina was to him. Relishing the familiarity of those words, even when directed at different people. "Sounds familiar," he said with amusement in his voice.

"Well, it's just surprising," she reasoned, leaning into Chuck's chest.

"I'm not surprised," he mused, seeing the familiarity of his relationship with Blair. "They met through a scheme, and ever since then, they've grown closer," he said as he took in Blair's scent, leaning against her. "Sound familiar?"

Realization dawned on Blair. He was referring to how they bonded over a mutual love for scheming and burlesque. It all started because of a dance at a burlesque club-Chuck's first real, successful investment and a limo ride home.

Back then she would never admit it, but that limo ride had been the best night of her life up to that point. The way he had looked at her with such yearning and devotion. He made her feel so loved like she was a goddess he worshiped.

The years that followed had been filled with both happiness and sorrow, and their love had been a complicated one, but she wouldn't change a thing about it. Because of it, she was here, married to the love of her life.

She could see the similarities between how her relationship with Chuck had started to that of Jack and Georgina, whatever they were at this point. Could their relationship blossom into love, and bring these two people together like it had for her and Chuck?

She pulled back from Chuck's warm embrace and looked up into his eyes. "Chuck, do you think we should help them?"

"How can we possibly help them? This is something they have to figure out on their own," he said in that husky voice of his that made her melt. "We can't interfere with everyone, especially with Jack and Georgina. Jack's my uncle and Georgina's his...something. They're both stubborn, but they'll figure it out."

"Do you really believe that?" she asked, crossing her arms, mulling the idea over.

"It did for us. It may have taken us a long time, but we did figure it out," he said with a satisfied smile. Not that smarmy grin she always pretended she hated. He wasn't smirking in the way the world was used to seeing, he was wearing a genuine smile, showing the gentle, sweet, loving young man she knew he could be. He was being her Chuck.

"True," she agreed. "But they're Jack and Georgina," she reasoned, searching for Chuck's hazel eyes. "They're more twisted than we are. And evil. Can we really forget what they've done to us in the past?"

"Blair," he said, looking into her eyes. "Part of that is my fault too" he tried to reason with her, remembering what he had done all those years ago. It had taken him a long time to become a man worthy of Blair Waldorf again. "He also brought us together for good. I can see he's trying to change."

"I'm not saying you have to trust him. It took me a long time, especially after everything he did to destroy us" he spoke calmly. "But if it wasn't for them I'm not sure we would be here today, happy. They saved us from prosecution and helped us get married. I can't help but feel I owe them for that."

Blair nodded silently, but still felt a bit hesitant. "But is it enough to forget everything they've done to us?"

Chuck cupped Blair's cheek affectionately before responding. "No" he admitted. "Nothing will ever be enough to forget what he did to us," he reasoned. "But," he took his hands in hers, rubbing them warmly, "But it would make them more bearable, and they wouldn't annoy us half as much, and maybe they might actually become tolerable? Plus, Jack's the only blood relative I have left after Bart's death."

Blair gulped at Chuck's last few words, sensing his unease at what happened between them and Bart. It still pained her to see Chuck so broken over the way Bart treated him in the last year of Bart's life. She knew Chuck was recovering one day at a time, but it didn't make things easy for him to deal with.

She knew Chuck was right. Jack was his only blood family left, and he had actually become somewhat of a decent uncle to Chuck, despite their past. So she would tolerate Jack, for Chuck's sake, if nothing more.

Which meant helping him get together with Georgina.

Maybe then he could actually become a decent person and not the egotistical Jack she was used to in the past.

"Okay," she agreed. "I will help them, but only because without them I'm not sure we would be here together." She placed her hands on Chuck's chest, feeling the heat of Chuck's warmth engulf her. "And for you, as he's your only blood family left, I can't fault you for wanting to build a relationship with him.

"I think in order to get them together we need to get them into the same room together somehow," she said as she went into scheming mode. "Why don't you talk to him tomorrow at Bass Industries, and I'll invite Georgina over for tea or something?" she gave a soft smile, before kissing Chuck sweetly. She was already mulling over a plan in her head.

"We just need to figure out where their heads are at before we decide what course of action to take," she said, beaming up at her husband, already excited over the idea of being able to scheme again.

"Let's just hope whatever plan you have cooking up will work," Chuck said, with warmth in his voice.

"Oh, it will" Blair thought with complete excitement. "We'll make sure of it." With that, she leaned in for a kiss, before taking her phone out and starting to put her plan into motion.

 ** _A/n: *Hides under a rock of been hiding under* So sorry for taking so long to post anything for gg. I've been busy with work, volunteer, going back to school, lost motivation. But I'm going to try my best and update more frequently after this story is complete. Yes, that's right, this story isn't complete yet. I'm in the process of doing the final edits of my final 2 chapters. This will be a three-shot. I would love to hear your comments and thoughts on, this is my first attempt at writing smut for Chuck and Blair in a really long time, and I wrote this last year, so I hope it's to your satisfaction. Please drop a review and let me know what you think because there's two more chapters to go which I'll post soon._**

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	2. The Plan

_**A/N: Here's another chapter. I tried to add more description here, and I hope it paid off.**_

 _ **Special thanks to my Beta Scarlett2U**_

 _ **Disclaimer: I don't own Gossip Girl or its characters. All Copyrights belong to its respective owners. Though I feel Chuck and Blair own me.**_

Chuck impatiently flicked his pen on his desk, lost in thought about the day's events. First, he had come home from a trying day at Bass Industries. The constant distrust of the company's board and shareholders was weighing him down. The upcoming Bass Industries gala would be crucial in securing their trust as their new CEO.

To add to the already troubling matters of his professional life, he knew his wife of six months was trying to find a suitable designer for her company. Blair was always talented, but he knew she preferred to be in control, taking command rather than putting the effort into designing herself. Her mother continued to push for her to hire Jenny Humphrey as her successor as the head designer and creative director for Waldorf Designs, while Blair would take the role of CEO-overseeing all operations and getting final approval of all the designs. Her mother would stay on as chairwoman of the board.

He understood Blair's reservations about hiring Jenny, given her history with the younger woman. He acknowledged that while she had forgiven him for his misdeed with Jenny and his many other mistakes, he wasn't as certain she'd forgiven Jenny yet.

It was so long ago, and he believed the only way for them to move towards their future was to let go of the past. That meant offering an olive branch, and letting bygones be bygones. He admitted he thought Jenny had potential as a designer; she could be a breath of fresh air for the company. Besides, Blair having authority over Jenny? He knew Blair would relish that. He also knew there was a time when Blair had held a deep respect for Jenny Humphrey, wanting to train her as her protégé.

Chuck always admired and worshiped Blair, like she was the most beautiful goddess he had ever gazed upon. This would never change. His relationship with Blair held so much more substance than that, though, it was on a much deeper level. He always encouraged her and supported her. She did the same for him.

He never felt an emotional connection with anyone the way he did with Blair. It made him feel like he had become worthy of her love and devotion. His wife taught him the meaning of love and what it meant to be loved in return, like his father should have.

He'd never be more grateful towards her for that. She made him whole, she kept him together, and filled his heart with hope and fulfillment. Without her, he was sure he would crumble into oblivion, drinking away his sorrow and succumbing to darkness. She showed him what she saw in him: she had known there was something arcane about him, but she chose to believe that there was a beacon of light that radiated in him. It just took falling in love with her for it to be discovered.

After Chuck and Blair had heard the argument between Jack and Georgina, they knew something had transpired between his coldhearted Uncle Jack and Georgina. Unlike Blair, however, he was not surprised. After all, like he and Blair, Jack and Georgina shared many paralleling qualities. It only surprised him they didn't find each other sooner.

That's when the two scheming rapscallions decided they were going to bring their counterparts together, for better or for worse. Chuck and Blair felt that subtly guiding them together in the end was the least they could do. Jack and Georgina had helped them make it to the altar in one piece. Chuck and Blair would have been suspected of Bart's murder, questioned by the police, and maybe not even received their happily ever after. They owed Jack and Georgina this at the very least.

To Chuck, it was beyond that. He wasn't always his uncle's biggest fan, but in these last two years, Jack really stepped up to help him. He was the one that brought him and Blair together again, and Chuck discovered something about his uncle in the process. He saw there was some good in him, even in tiny doses, that was something worth fighting for. In the past, Jack was driven by jealousy and revenge, but now he saw a side of his uncle he hadn't been aware of. He saw a man with a fragile and broken heart, a heart that had been frozen by hatred and jealousy. He came to the realization of the cause: Bart Bass.

His latest discovery about his uncle didn't exonerate or justify his actions towards him and Blair, but it gave Chuck a flicker of hope Jack could be saved and find happiness, something he wanted for his uncle. Maybe then Jack could finally be happy, and not try to absorb it from others.

He was already forming a plan in his mind. All he would need was to get Jack and Georgina in the same room and get them to realize the fire blazing between them.

Just as he pondered over the plan, he heard his door being swung open and his uncle came bolting in, like he owned the company instead of Chuck. "Chuck!" his voice reverberated into the room. "Where are the documents that needed your signature to move forward with the hotel acquisition in Switzerland?"

Chuck leaned forward in his cozy leather chair and signed the documents. The ink blotched onto the papers, finalizing the deal for the project.

"The negotiations in Switzerland are finishing nicely," Jack added for good measure. Ever since he joined Bass Industries as Chuck's COO, they had developed a good business relationship with their international investors. The business thrived with Jack's involvement.

Some of Chuck's investors still held misgivings about having a young billionaire with an abhorrent reputation leading his father's Empire. The man Chuck had been was a stranger to him now. However, when investors refused to conduct business with him as a result of his past, Jack stepped in and swayed them over to their side, assuring them it was a sensible business decision. Jack and Chuck became a force to be reckoned with in the business industry, even rivaling Donald Trump in real estate.

"That's great to hear, Jack," he said, locking eyes with his uncle. He knew getting straight to the point would be the best move. He leaned towards his desk in his office, smiling over his plan.

It was ironic that his office had once had an ominous feeling, when what he needed was an atmosphere of light and clarity. He removed all pictures of his father that adorned his office. It was like Bart never occupied this office, like he never existed between these walls. Chuck repainted the walls an opaque purple, and replaced Bart's pictures with photos of him and Blair together. Beside them were pictures of the whole Non-Judging Breakfast Club.

Chuck decided it felt liberating being reminded of pleasant memories of the people who actually loved and cared about him, rather than being plagued by the memories of a father who didn't give a damn about him and tried to murder him in cold blood. The thought of Bart trying to murder him still sent a shiver running down his spine.

"But that's not why I called you here."

Jack's eyes immediately sought Chuck's as he studied Chuck's expression. "Oh, then what could we possibly have to talk about, Chuck?" Jack didn't mean to sound dismissive, but he was caught off guard at Chuck's brusqueness. It was the coping mechanism Jack resorted to when he felt cornered by Chuck's direct approach of conversing. Chuck never discussed anything but business and his marriage to Blair with Jack. It became a regular conversation, and that's what he always expected from Chuck. He had a sinking feeling about this.

"About you," Chuck elaborated further, hoping he gained Jack's full attention.

Luckily, he succeeded.

"Me?" he said, blinking his eyes in surprise. Of all the things he expected, this wasn't one of them. They never discussed Jack's personal life. Maybe it was about his performance at Bass Industries, or a client Chuck needed him to secure.

"Yes, Jack," he continued. "This may come as a shock to you, but I do care about you," he spoke calmly. "For example, I'm particularly interested in your relationship with Georgina Sparks."

"What about me and Georgina?" he asked, taken aback at the direction of conversation. How did he know? Did Chuck overhear their argument at the Bass townhouse the other night? Jack assumed they would be in the clear. He suspected Chuck and Blair wouldn't be home for another hour or so when they arrived at his penthouse.

Jack concluded Chuck and Blair would be hanging out with Nate and Serena. Chuck told Jack he was welcome to come to his place whenever he wanted, or if he needed anything. Jack knew he abused that privilege at times, but Chuck owed him after he saved his ass from being prosecuted for his dear brother's death. When that kind of opportunity presented itself to you, you utilized it to its full capacity.

"Jack, I know you haven't always thought much of me," he stated knowingly, "But don't take me for a fool. I witnessed you and Georgina...arguing," he said, stressing the word arguing, implying he knew exactly what was going on between them.

"Your point is?" he said impassively.

"My point is there's something going on between you two, and it would be a waste not to explore it," Chuck tried to convince his uncle.

"And what?" he said mockingly. "You think I'll become like you? Tender-hearted?"

Jack's words slashed through his heart, sending a chill rippling through his body, hitting him more violently than a slap across the face. The way Jack mocked his relationship with his wife still sent irritation burning through his veins.

Jack hadn't always waved the Chuck and Blair fan banner, and yet the way he constantly disparaged his love for Blair with contempt caused Chuck's annoyance to elevate. He was still haunted by the mistakes he made with Blair and a big factor was Jack's manipulation. Chuck hoped they left any hostility they had in the past, but maybe he was wrong.

Jack was blinded by the depths of what he felt towards Georgina, just like Chuck would always be irrevocably in love with his wife. Chuck could feel the tension blistering between them miles away, and it stunned him how oblivious his uncle and Georgina were to it.

Would they see it?

Or would their pride get the better of them?

He never thought he'd be plotting for his uncle's happiness, but that didn't hinder him from his plan. Maybe it was Chuck's fiercely loyal and forgiving nature, even when people let him down. Jack always taunted him, and yet Chuck glimpsed him, and discovered something redeemable. He believed Georgina would be vital to thawing Jack's frozen heart.

It was imperative getting Jack to discover and hone that to its full potential.

"You say that like I can't still be a force to be reckoned with in this business, as if I'm not the same Chuck you've known all this time," he stated with mock-hurt. "I'm still me, Jack. I can still be a successful businessman who can be a force to contend with. I can still tear my enemies apart with my art of scheming," he prattled off, hoping he was getting his message across.

"Yes, but Blair's changed you," Jack stated, disappointment flashed across his face. He remembered the careless, manipulative Chuck he'd known before his return to New York, after his dear brother's death.

"And that's a bad thing?" he inquired. "Look, Uncle, it's no secret I'm not the careless, debauched, misguided kid you knew in my early teens, but that's a good thing. It means people matter to me and I matter to them. It shows that, underneath my cool exterior, I do have a heart, but I'm still a force of nature. Hurt my friends or family, and I'll show them what the name Chuck Bass means. It means I utilize my art of scheming for what is important, not for mindless games and manipulation like I used to. That Chuck was an empty shell, now I feel –"

"Whole," Jack finished the thought. "And while that's a lovely speech, Chuck, I'm just not sure it's for me. I'm not like you. I don't care about people like you've grown accustomed to. I only fuck whatever's in my line of vision then move onto the next girl. I can't be what everyone expects me to."

"Would that be such a bad thing?" Chuck asked with sincere curiosity. "Jack, you've been lonely for a long time; maybe Georgina can finally bring some light into those eyes of yours," Chuck tried to reason, hoping his words were persuasive.

"Except you're forgetting something, nephew," he looked lazily into Chuck's eyes, indifferent to his sincerity. "She's made it clear I mean nothing to her."

Chuck let a hysterical laugh escape his mouth. "And you believed that? I'm surprised. Do you know how many times Blair fed me the same line when she didn't want to admit the truth, when she decided to run away from what she truly felt?" he studied his uncle's impassive expression. "Georgina wants you; she – just doesn't know it yet."

"Don't you sound confident?" he mocked, laughing.

"You forget, Jack, I lost my virginity to her, and I've known her for years," he pointed out with a cocky grin etching his features. "So I know a little bit of how her head works. She may be twisted, but so are you. In a way, you two are a perfect match made in hell. Look, Jack, she wants you to fight for her, she wants you to show her you're willing to fight for her and not give up. She wants you to prove that you're the one."

Jealousy burned through his veins like acid at the mere thought of Chuck being Georgina's first. He tried to control his jealousy and not let it cloud his judgment. He knew Chuck never felt anything towards her, and realized he had nothing to worry about.

He recalled the precise moment Georgina told him about Chuck and Georgina's one-night stand. It was after Jack and Georgina got to know each other better, when they started to form a friendship. She had been ranting about Chuck and Blair's new marriage, and she revealed her past with Chuck to him.

Jack's features had scrunched up at Georgina's reveal, as if he didn't want to hear any of it. Jack had known about Chuck's womanizing past, but he didn't know that Georgina was what started it for Chuck.

Just the thought of Chuck taking Georgina's virginity made Jack envious of his nephew. Chuck didn't have the most reputable reputation, but to discover that Georgina was the beginning of Chuck's lifestyle surprised him.

Every time Jack got to interact with Georgina, he discovered a different side of her. It showed him how strong she was. He wondered if this was the reason Georgina had settled for Philip. She didn't appear to love him from what she saw of their interactions. He was like a minion to her, always doing her dirty work.

Chuck understood Georgina's mindset. It's the same one he witnessed with Blair, but he never gave up on her. It was only when he believed someone could make her happier that he let her go, he realized with a rush of sadness. The painful memories started to cloud around his head, unwilling to rest, even though they'd forgiven each other. Those memories never let him forget all the bad things he had done, but they also molded him into the sweet, loving husband he is now.

Even after six years, those butterflies still bloomed just as fiercely in the pit of his stomach as when he was a lovesick teenager noticing his desire for Blair the first time., He never gave up on her or stopped loving her, and never would. He'd love her until he took his last breath. Nothing would change that.

He hoped Jack would experience that kind of love soon. Maybe it would guide his uncle towards the light and lead him towards the right path. It was his belief Georgina could be vital to achieving this goal, even as crazy as she'd been.

"Georgina's exactly what a man like you needs, Jack," he continued on, causing Jack to roll his eyes. Chuck knew the expression Jack wore all too well. He usually displayed it when he was irritated by Chuck, or trying to convince everyone he was better off alone.

Once upon a time Chuck might have believed it too. Before he discovered what happiness meant, when he learned the meaning of love. When he believed that happiness wasn't meant for people like him. The thought seemed irrelevant now, given how jubilant he felt with Blair.

Chuck knew better now. Happiness didn't come easy, and it certainly wasn't a walk in the park. You had to fight for that happiness-stare it straight in the face and never lose sight of it, keep fighting until it's within your grasp.

"Please, Jack Bass doesn't need anybody," Jack scoffed, disbelief flaring in his hollow voice.

"Everyone needs somebody," Chuck said, spurn surging through him like thunder. "Even you. This act of how you don't care about anything or anybody is getting old, don't you think?"

Jack grinned cockily. "Because I don't," he clarified with the venom of a snake.

"You'd sound more convincing if you didn't show signs that you care," Chuck stated with a light smile. "You helped me and Blair, when you didn't have to, uncle. That shows the opposite of the heartless monster you make the world believe. The only person you're fooling is yourself."

Jack searched for a retort at the tip of his tongue, something snarky to slip out, but his voice faltered.

"Because you know there is a part of you that cares, and wants Georgina. Which is why we have a plan," Chuck said, an idea already coming to the surface of his mind, hoping it would pan out.

"You and Blair are scheming again? Don't you have anything better to do? One would think newlyweds would have better things to occupy their time," he mused with an arched eyebrow

Chuck ignored Jack's comment and forged ahead. "I'd like you to accompany Georgina to the annual Bass Industries gala," he revealed. He thought his plan was ingenious; he was hoping it would glitter with success by the end of the night.

"Well," Jack began, a smirk stealing across his face. "I may not be as convinced as you are that I love Georgina, but the idea of getting into Georgina's pants again sounds very tempting."

"You're kidding yourself if you think this is only about sex, Jack. She means more to you than any girl you've been with, even if you don't see it yet," he cajoled, hoping his voice didn't betray how he actually felt, and that it sounded inspiring. "But you'll both see by night's end."

"We'll see, Chuckie," he said as he waltzed out of Chuck's office.

'Oh, you will' he decided as he sent a text to cue Blair in on the plan, a grin lighting his face.

.

.

.

Blair sat in their spacious living room with her shapely legs crossed one over the other, reading her cell phone, when she was alerted to a text from her wonderful husband. It read:

 _I have a plan, my Queen. Do you think you can get Georgina to agree to accompany Jack, arm in arm tomorrow evening?_

 _-C_

Blair smiled, awaiting Georgina's inevitable arrival andadmiring the place she called their home. Natural light flooded into the roomy living room, and a tranquil feeling pervaded the space. It tasted of the opulence that Chuck and Blair always desired.

After Chuck and Blair got married, they knew they desired children in their future, and so decided to purchase their own home. One that would be child-friendly and one that spoke their language in elegance, and that meant leaving Chuck's Girl Scout painting and his bachelor best friend Nate behind.

Chuck knew Blair would never consider moving into the Empire after their history with the hotel. They wanted a home that would scream Chuck and Blair, and suited their tastes. They passed on the Waldorf penthouse, as Blair didn't want to face the awkward moment her mother could walk in on them in an intimate moment, or have her mother's shadow looming over her.

They hired a realtor to scout their home, one on the Upper East Side, they stressed to their realtor. They were thrilled with their luck when they found their new majestic home within two months of searching and made a lavish offer to the owners, not sparing a dime.

It was impeccable. The colossal home left space for Chuck's home office, and Blair to assemble an atelier for her designs at Waldorf. They liked the welcoming light that surged into the home. They couldn't ask for a more elegant home that suited their desires.

As the memory flitted through her, she heard the clicking of heels on her marble floors, indicating Georgina's impending arrival as she bolted into her living room as if she owned the place. 'Here we go,' Blair grumbled to herself as she greeted her former-nemesis-turned-tolerable-acquaintance.

"Georgina, how nice of you to join me for tea," she flashed her brightest smile. Truth be told, she never enjoyed the bitter taste in her mouth, or the repulsive smell that filled her nostrils in its presence. It never suited Georgina's tastes either, but Blair knew she would be intrigued by her invitation, enough to meet her and see what she was planning for herself.

"Well, I knew tea wasn't really on the menu," Georgina smirked knowingly. "So I had to see what was so important that Queen B herself decided to grace me with her presence."

Blair's smile faltered with Georgina's harsh words, which burned like acid. She glanced Georgina's direction, noticing the sour look Georgina was bombarding her with.

Blair and Georgina had always had a truculent relationship, and with good reason, she added silently to herself. Georgina's main motivation was always rooted by revenge and her thirst for absorbing Blair's happiness, and yet for some reason, Blair wanted to help her.

It took every ounce of self-restraint to execute the plan, and not just leave Georgina to her own devices with Jack. As much as Blair hated to admit it, Georgina and Jack had helped Blair and Chuck out of an arduous situation.

"Not everyone has an ulterior motive, you know," she shot back dryly, wanting to get straight to the point.

"True," Georgina agreed, "But you? I know you, Blair; you're the Queen B. You ruled the school with an iron fist. How am I supposed to believe there's no ulterior motive behind this invitation for tea?" she said, stressing the word tea with air quotes.

Blair blanched at Georgina's supposed innocent façade. "Don't play innocent, Georgina. We both know you caused a lot of damage to me and my friends over the years," she declared, deciding to get to the point, "but right now I just want to know what's going on between you and Jack?"

"Jack?" she echoed, her voice honey sweet. "You wouldn't happen to mean Jack Bass, would you?"

"Deny all you want, Georgina," she interjected before Georgina could deny what she knew was going on between Georgina and Jack. She knew what could happen with that attraction if it went unquenched. It would inflame your senses until your skin burned with desire.

She felt the same way about Chuck. She denied the magnetism that drew them towards each other, to the point the desire burned like a volcano and she found herself being drawn to him with more flaming desire. You could only resist for so long before it eventually consumed you.

Blair saw the way Georgina and Jack looked at each other, realizing it extended further than desire. Blair noticed their tacit understanding of each other, and knew it rooted deeper than just sex. The sight of their stolen glances was telling enough, not to mention the blazing rage surging through Jack's eyes when Georgina dismissed the idea of them. She'd experienced that with Chuck when they misguidedly told themselves they hated each other. It was just an excuse for them to engage in passionate lovemaking, fueled by faux hatred.

Blair saw Georgina's facial expression had turned arctic cold. "Not that it's any of your business, but why do you care?"

"Georgina," she murmured. "I know you and I haven't always gotten along—"

"Understatement!" she interjected, keeping Blair from articulating her words.

"But," Blair continued, "I've always thought of you as a worthy adversary, and I must admit, these past six months you've come through for me and Chuck."

"And you think because I helped you and your adoring Chuck that we're friends? Just because I helped you out one time, which I might add was out of obligation more than anything, you think that somehow means that I have to force myself to like you?" she bitched back.

"Of course not," she tried, before Georgina once again cut her off.

"Face it, Blair, we'll never ever be friends. We're too different. What makes you think I want to discuss Jack Bass with you, Blair?"

Blair smoothed her hands to her face before responding, "Because, Sparks, our goal happens to align!"

"Oh, and what may that be?" she asked, as if the idea was alien to her.

"I can help you get Jack," she confirmed.

"Can you now?" she smirked. "What makes you think I want Jack or need your help?"

Blair felt Georgina's facial expression soften at the idea of Jack's name being mentioned. She knew what that meant. She had a soft spot for Jack Bass, and Blair would utilize that to her advantage.

Georgina was always a tough one to placate, but she now had a weakness, one which would benefit both of them. If she succeeded in Operation Jackgina, maybe they would become so entangled in each other, they wouldn't drain their time as much, just simply become wrapped up in each other, and she wouldn't have to worry about them interfering with her and Chuck. Lately she and Chuck had been trying to assert themselves professionally, so they came home exhausted, and Jack and Georgina often came barging into their home whenever they deemed it a necessity.

"Because, Georgina, I've been there before," Blair said, a soft smile forming on her features, as she recalled the memory of the beginning of her relationship with Chuck. She shifted in her seat imperceptibly at the memory. "Just know this, Georgina: Denial will only work so long before it consumes you. I tried it for years, before I no longer could deny how I felt. I've seen the way you look at each other. It's the same way Chuck looks at me. Deny all you want, but you know it's the truth."

Georgina avoided Blair's gaze, trying to dismiss what Blair was telling her.

Did she have feelings for Jack? She tried to tell herself she didn't. But what if she'd been lying to herself all along so that she didn't get her heart shattered. Because, at the end of the day, it wasn't just about her, it was also about her son Milo.

Georgina was never the gambler in relationships. But somehow the idea of Jack made her feel like she was putting everything on the line. She'd never taken a chance with her heart like this before. Her men either were spoken for or were safe options. Jack would be the biggest gamble her heart would ever risk.

Would Milo like Jack? Would he dislike Jack? The questions kept spinning over and over in her head until it started to overwhelm her with doubt. Some advice from the Queen B herself might help, right? After all, she denied how she felt about Chuck for so long. Blair was in such denial that she married a foreign prince and later ran towards Humphrey in her continuous denial to get over Chuck. Maybe Blair was right, and she could only deny Jack for so long before her willpower withered.

"What if Milo doesn't like Jack?" she asked, her eyes brightening slightly at the mention of Milo.

That's when it hit Blair like a hurricane-this wasn't just about Georgina, this was also about Milo, and if she could accept having another potential stepfather in her son's life.

"He liked Philip," Blair reminded her, hoping to put Georgina at ease. In truth, she understood Georgina's fears. If Blair found herself in Georgina's position, she would be just as wary.

"Yeah, he did," she agreed, locking eyes with Blair. "But Philip was too nice. He could get along with anybody. Jack, on the other hand…."

Blair relaxed over Georgina's concerns of getting involved with Jack. If the roles were reversed and someone tried to set her up with Chuck, assuming they hadn't known each other as long as they did, and she had a child, she herself might have the same doubts.

"But what if he does, and he gets along famously with Jack?" she questioned, hoping that would be the case. "What if it is exactly what Milo needs?"

Georgina looked puzzled. "You do realize this is a Bass were talking about, right? And Jack Bass, no less? Have you forgotten all the things Jack did to you and Chuck?"

Blair flinched at Georgina's statement, all the memories came bombarding into her mind. Had she forgotten all of Jack's transgressions? No, but she knew how important Jack was to Chuck. He was the only blood-related family Chuck had left, and she couldn't take that away from him.

She searched her brain to find a response that would ease Georgina, but came up empty-handed finding a suitable response, so she opted to be honest instead. "No, I haven't forgotten. But I know how important he's become in my husband's life, and so that makes him important to me."

Georgina's eyes started to flicker, glancing up at Blair and considering her words. She felt the need to ask Blair the question she'd been dying to ask for quite a while. "How did you know Chuck was the one, Blair?"

Blair's eyes shot up in surprise. She never expected Georgina to strike up a conversation with her, much less about her husband. She felt the resolve to answer her with honesty-she owed Georgina that much, didn't she? She let out a soft, tranquil sigh. "I didn't at first," she began to explain, "Like you, I tried to deny it with every fiber of my being. I tried to run away from it, I tried to kill it, hoping the feeling would go away."

"But it didn't, did it?" her eyes glazed with piqued interest, wondering if she was doing the right thing considering Blair's offer, knowing Jack's reputation. Maybe hearing how everything worked out between Chuck and Blair might give her a liberating feeling from the imprisonment of her own self-doubt.

"No," Blair conceded. "Loving Chuck was never easy, Georgina. He was a difficult man to love." She observed the way Georgina's eyes shone with curiosity. "But he was incredibly loyal, he refused to give up on us, and he even gave me another chance after everything I put him through the last year," Memories of those days began to give Blair an unsettled feeling, as the memories began to deluge her mind.

Everything.

Blair almost having a baby with Louis, a man she thought was different, but was just a copycat of the old, darker version of Chuck. She loved all parts of Chuck, and didn't want a replica of him in Louis. As time went by, she realized her feelings for Louis had waned, while her love for Chuck was flourishing with each passing day.

He tried becoming a better man; not because of her, because he wanted to for himself. That meant something special to her. The fact he did it for himself, and not as a tactic to reclaim her heart, showed how far he had come.

She nearly threw away another chance with Chuck when she shackled her life to Dan Humphrey instead of giving her true love another chance. When she was with Dan, she felt confined to his world, but with Chuck she felt liberated.

She didn't think she was ready to admit the way she still loved Chuck, still feeling the ardent passion for him she always did. She worried what reuniting with Chuck would really mean. What if she lost him again?

But she was foolish to think that.

Dan never loved her, he only acted like he did. He loved the part of her he constructed in his book. If he truly loved her, he wouldn't expect her to change, he'd accept her the way Chuck always did.

Chuck, in spite of all it, forgave her and continued to fight for her. And it was like being freed from the chains of a loveless relationship. She was free. That's how she always knew Chuck was the love of her life. He never renounced their love, he always fought for it, refusing to give up. Even when the darkest things conquered them.

"Chuck was always a gamble, but we refused to give up on each other," she continued, her eyes gleaming with joy as she talked about Chuck. "The way he made me feel, like there was something blooming in the pit of my stomach, fluttering uncontrollably and refusing to die."

"Butterflies?" she mocked. "The great Queen B feels butterflies?"

"Mock all you want, Georgina," Blair spoke with irritation, "But when it happens to you, you'll understand what I mean."

"So, what did you have in mind then?" Georgina asked heedfully.

"How would you feel about accompanying Jack to the annual Bass Industries gala?" she said with enthusiasm.

"Why do I have a feeling you won't take no for an answer?"

"Oh, Georgie, you know me well," Blair smiled confidently.

.

.

.

 _ **~~To Be Continued~~**_

 _ **A/N: So how did I do with this chapter? I wrote a little from Jack and Georgina's POV to explain their motivations a bit, I hope it worked. Would love to hear what you think. One more chapter after this.**_


	3. The Gala

**_A/N: The final chapter is here. I hope you enjoy._**

 ** _Disclaimer: I don't own these characters. All copyrights belong to their respective owners._**

 ** _Special thanks to my beta, Scarlett 2U_**

Jack strolled into the elegant ballroom, arms laced with Georgina Sparks. When he agreed to accompany Georgina, he'd anticipated she would look stunning, but the way she looked now was…breathtaking. He craved Georgina like a man craved oxygen, as much as he hated to admit it. She looked exquisite.

God, what was she doing to him? He started doubting himself around her. He felt out of place in her presence, and what surprised him most is how she made him feel. She made him question every decision he ever made. He felt his heart hammer in his chest violently from just thinking about her.

His arm twined around her waist, pulling her closer towards him, arriving at the entrance of the ballroom floor. Bass Industries held a gala at the Palace every year, as per tradition. Chuck would use this event to exult his success at the helm of Bass Industries, and gain support within the board and its shareholders. Given that some shareholders still firmly believed Chuck murdered Bart, Jack knew all eyes would be on him and Chuck and they needed to prove themselves to the company's stakeholders.

Jack wasn't always Chuck's biggest fanboy, something the public was cognizant of. But in these past years, they had grown closer. They both knew they needed to join forces to destroy Bart. He'd kicked them both out of Bass Industries to conceal his secret dealings. During this time, they developed a detente with each other. They realized that Bart, and not each other, was the real enemy. Working together collaboratively to ensure Bart's demise was the smarter plan to ascend to the throne of Bass Industries.

Over time, Jack started to appreciate his nephew's talents in the business world, and understand him extensively better. Both he and Chuck were underappreciated by the ruthless Bart Bass. They'd been expendable, nothing more than a pawn Bart needed to knock off the chess board to reclaim the power he once infused.

With the nightmare Bart Bass posed, Jack and Chuck established a partnership and began to appreciate each other. Jack observed Chuck's relationship to Blair Waldorf, now Bass. He studied the way they interacted with each other, how their eyes sparked when they were in the same proximity, and that's why, without a shadow of doubt, he knew. Chuck did indeed love Blair Waldorf, and he regretted the mistakes he had made in his past. It was then Jack began to grasp the enormity of the role he played in nearly destroying Chuck's relationship with her. Chuck forgave Jack's past treatment of him, but he wasn't a fool. He knew Chuck wouldn't forget, and had to gain his trust. Something Jack was prepared to do.

Chuck stressed the importance of this gala for the future of Bass Industries-and Chuck's role at Bass Industries. The future of Bass Industries all rode on how tonight went.

Currently Jack's sole focus was on Georgina. He gazed into her aqua blue eyes, smiling crookedly. "Well, I must say, Sparks, you look glorious in that dress."

Jack let a genuine smile flash across his face when she chuckled in response. Georgina looked exquisite in her crimson red dress, a Waldorf original that Blair chose precisely for this occasion. The dress hugged her curves perfectly, and it took all his restraint not to take her to one of the guest rooms and peel it off her.

He didn't remember a time when anyone could inspire this kind of feeling in him. He had become enslaved to his own emotions, and it was driving him insane. Was Chuck right? Could he feel something towards her that far exceeded that of a sexual nature?

Georgina's smile glistened and her eyes sparkled as she took in Jack's appearance. He'd donned a tailored Hugo Boss black suit, matched with a snow white dress shirt and crimson red tie. He wore a matching pair of pants, and Georgina's eyes darkened with desire. "Well, you sure look dashing, Mr. Bass," she hummed appreciatively," But that must be a Bass trait."

Despite his growing jealousy at her statement, knowing what she was insinuating, he couldn't help but generate a smile. Mere water under the bridge now. Georgina had meant it as a compliment towards Jack and the unmatched style of his family.

Jack and Georgina met with some of the Board to broach Bass's future and Chuck's leadership. He tried to ease their concerns about Chuck's leadership. He hoped Chuck's speech would bring their worries to rest.

The room paused when they heard Chuck being announced onto stage. The crowd applauded at Chuck's entrance. Friends, family, investors, and Board members were in attendance. He knew some of them still raised concerns, but hoped Chuck's speech would diminish them.

"Thank you," Chuck started, trying to find his voice. "I want to thank everyone for coming here tonight. When I was reinstated at the helm of Bass Industries, I wanted to rebrand the company my father built from nothing."

All eyes were turned on Chuck, taking in his appearance. He wore an Armani suit, with a sky blue dress shirt and a light silver tie, displaying his confidence to the shareholders. They looked upon him with curiosity.

"As you know, Bass Industries hasn't always had the most ethical business practices," he went on, gaining the attention of the throng of people listening and watching intently. "But, under my leadership, I hope to change that. I want everything to be done by the book, and ethically. I won't run the company like my father. I don't want to be like him. I hope to set a new direction for the company while keeping the integrity Bart had built from nothing," Chuck glanced at Jack, then his wife intensely. "But I wouldn't be here if it weren't for my wife's support, and my uncle and stepmother's guidance and support at the company. Having my wife's encouragement and support, Lily's guidance, and my Uncle Jack as my right hand has helped shape Bass Industries into a company I can be proud of. Here's to another prosperous year at Bass Industries."

The assembly of people applauded thunderously after his speech, then the guests were invited to dance with their significant others. Chuck danced with his wife, and Jack saw a sparkle in Blair Bass's eyes being in her husband's embrace.

In this moment Jack knew he yearned for that happiness. Jack guided Georgina to the dance floor, as he knew Chuck and Blair expected from him. He'd be lying if he didn't find glory in that. The whole night he couldn't get Georgina out of his mind. All thoughts seemed to come back to her. He felt his heart race wildly in her presence-an effect no woman had on him before, no matter how enticing they were.

Jack was impressed how Chuck presented himself. He displayed a confident demeanor that spoke reverence. He illustrated integrity that Bart lacked. His dear old brother was infamous for finagling the business world to suit his own design, not giving a shit about who he trampled in the process. Most who opposed him were doomed.

Chuck strived to make his mark professionally. He preferred to follow proper procedure, not wanting to resort to the corrupt attitude as Jack's dear brother, and he applauded him for it. He knew Chuck would thrive at the throne of Bass Industries with that benevolence.

But success in business was not everything. He realized he wanted what Chuck had with Blair, no matter how he tried to ignore and deny it. He wanted someone who made his eyes sparkle with joy, someone who caused his face to curve into a genuine smile, not the faux cocky grin he usually sported. He wanted someone who understood him the way Chuck and Blair understood each other, and there was only one woman who fit that bill.

Georgina Sparks.

Georgina was remarkable in every sense of the word. She was manipulative, conniving, calculating, and the same brand of crazy he was. Above all, she had everyone's back who received her loyalty, and was deserving of it, and was fiercely strong.

Jack dragged her towards the dance floor, placing his hands on her hips as they swayed to the soft melody of the jazz music, moving to the rhythm of the music. "That was quite the speech my dear nephew made, wasn't it?" he praised sincerely.

He and Chuck weren't always the best of friends, but circumstances brought them together, and he took joy in getting to know and understand him better. Jack now understood him better beyond the carefree playboy billionaire of Chuck's youth, appreciating his complexity and growth.

"And Blair had nothing to do with that, I'm sure," she retorted dryly. "We both know he wouldn't be who he is without her."

"I used to think the same way," he agreed, "But I've recently realized that sometimes change isn't so bad. Plus, you know the way Chuck was before."

"True, but seeing them all lovey dovey can be nauseating," she tried to get Jack to see her point.

"Maybe you're just jealous Chuck finally found someone to make him happy that isn't you," he began to rock her back and forth to the hum of the music, as he tried to get Georgina to see his perspective. "Look, I haven't always been their biggest fan. I almost destroyed them, after all, but I noticed Chuck seems almost human in her presence; she inspires him to be better."

Jack continued swinging her hips back and forth, getting lost in her beauty, and her annoyance talking about Chuck and Blair.

"Enough about Chuck and Blair," she said, disinterested in the current conversation, "Let's talk about you."

"There's not much to say," Jack shrugged with a bored tone. Truthfully, Jack didn't find anything about himself being conversation-worthy, but these last several months he didn't find himself worthy of anything, not since he realized the enormity of what he'd done in his past.

Georgina leered at him seductively. "Come on, there must be something interesting to say about the elusive Jack Bass I've heard about? There must be something you want in life," Georgina pressed, hoping she could figure out if Jack wanted what she desired.

"The thing I want most…," Jack said ruefully, "I've come to realize I don't deserve to be graced with her presence."

Georgina froze at the magnitude of Jack's words. She knew Jack didn't have the most stellar reputation, especially when it came to his nephew, or his whole family for that matter. Jack was no Philip, and that's part of what drew them towards each other. She didn't want a boring trophy husband who caved to every request on a whim.

She wanted someone that brought her adventure, excitement and someone who challenged her. someone that made her blood pulse with desire. Someone who gazed at her like she was the most beautiful creature in the world. Why couldn't he see that?

Before she could protest in words, his stony eyes peered into her blue orbs until they held his gaze. "My whole life I never cared who I had to hurt to get ahead of the game," he explained, "I never cared who I had to hurt, even my own blood," he went on, continuing to examine her eyes. "But somehow I've grown to care about my nephew these last couple years. I've also become enthralled by you. All I know is the idea of seeing you sad makes me want to see you smile instead."

Jack felt a weight being lifted off his shoulders. Jack had always lied to suit his agenda, but the thought of lying to Georgina never crossed his mind. He started suspecting Chuck was right, and he was falling for Georgina. As if he were being possessed, with no control over his sudden emotions and feelings.

Was this how Chuck felt every time he was near Blair? He now understood Chuck more than he would care to admit. He knew every time he saw Georgina he felt his heart race.

"Jack…" she tried, before Jack interrupted.

"The truth is, you're the most gorgeous woman I've ever met," he said charmingly, "You've completely captivated me, and I don't know what to do about it. Because I know I don't deserve you, not after everything I've done."

"What you've done is in the past," she reminded him. "Chuck's forgiven you. Blair's always held grudges, but she's willing to tolerate you for Chuck's sake," she prattled on. "You have grown up, you aren't the same bitter, jealous Uncle Jack you were. I just wish you could see it."

As Jack let Georgina's words sink in, he started to contemplate what Georgina said, and they continued dancing to the soft melody of the music.

"I have a lot to make up for. But I want to try," he amended, trying to find the words. "Now, let's say we talk about more interesting topics. What are your hopes for the future?" Jack pressed. He wanted to know what she aspired to be in the future. He wanted to know her better.

"Publishing has a certain appeal to it," Georgina smiled. Georgina never thought much about her future, but since she started helping Dan write his tell-all novel, she found publishing interesting. She thought about how she could help other authors.

"Gossip Girl certainly had its appeal, didn't it? All the gossip, and now you can't help but dig your claws into more gossip," he laughed with amusement. He had been made aware of her brief stint as Gossip Girl, before handing it to Serena, and then back to that Humphrey kid.

He had to admit Georgina managed the site with an iron fist, much better than Serena ever did-heck, she even rivaled the original Gossip Girl. Serena was too obvious as Gossip Girl, always targeting those outside her social circle; it held a certain bias to it. Something you couldn't do as Gossip Girl without being caught. To top it all off, she tried replacing herself with her cousin/half-sister, as if that wasn't obvious for what she was trying to achieve.

Dan had the intelligence to pull it off. He was on the outside, despite his connections with the elite, but didn't have the stomach for it when things got bumpy. Not that Jack blamed him.

Georgina, on the other hand, knew how dirty being Gossip Girl could be, and only signed it away because she grew bored with it, not because she couldn't handle it anymore. She had the brains and stomach to be convincing as Gossip Girl, and that made him proud of Georgina's accomplishments.

Could Georgina have ignited a passion for Gossip, and publishing in general? If it wasn't for her brief reign as Gossip Girl, he wasn't sure he could picture it. Now, however, it seemed to fit like a puzzle. Jack was a resourceful man; perhaps he could help get her foot in the door. "You know, I know some people that could help with that?" he offered, liking the prospect of Georgina achieving her goal.

Georgina beamed at Jack's generosity, but this was something she had to do on her own. She appreciated his offer, but how would it look if she achieved her goal because of her connection to the Bass family? She couldn't be a reflection of the most prominent family in New York Society, she had to take New York by storm. "While that's a tempting offer, Jack, this is something I have to do on my own."

Jack nodded in response, completely understanding her perspective. Jack never felt good enough at Bass Industries under his brother's rule, but with Chuck reigning supreme at Bass Industries, he felt different. He felt Chuck was giving him a second chance with the company and listening to Jack's concerns and ideas.

He understood wanting to achieve something on your own. Jack wished he did that himself long ago, but now he made the most out of it, and used his talents to his full potential to help Bass Industries flourish.

"What about you, Jack? Do you see yourself working in another field, or working beside Chuck in years to come?" she inquired with piqued interest.

Jack never thought about it much if he was being truthful. He was more of a 'cross that bridge when I get to it' kind of man. He never looked far ahead in the grand scheme of things, he lived in the moment. "I haven't really decided yet," he said with honesty.

Did he want to stay at Bass Industries, the company where he'd felt like an outcast under Bart's thumb? Or did he want to let his talents radiate elsewhere? He decided he could discuss it with Chuck, and maybe he try to convince him to stay. He grinned at the thought Chuck needing his help to keep Bass Industries in its current glory.

Georgina seemed to accept his answer, as she moved her hands towards his hips, rocking back and forth rhythmically as the music pounded into his ears. "Jack," she started, trying to locate her voice "I just wanted to apologize for yesterday," she finished, relief flooding through her like a tsunami. Maybe after today, they'd finally move forward.

"Apologize? "he asked, taken aback. What was she apologizing for? Confusion swirled around his head faster than he could form a response. He didn't know what she could have possibly done to garner an apology to him.

"Yes," she whispered. "About yesterday. I knew after…what happened between us, there was no way that I could be okay with just being your friend, so I panicked and shut you out. "

Understanding clicked in Jack's mind. She was apologizing for their argument at Chuck and Blair's home, when they both said harsh things to each other. He couldn't blame Georgina for shutting him out. He wasn't exactly Prince Charming. He wasn't the kind of man you brought home to your parents-or in Georgina's case, son. Jack was a diabolical man, as was Georgina, but he knew she wanted to be better for Milo. She had more than herself to think of. Was she concerned about him not being good enough for Milo?

"This is about Milo, isn't it?" he inquired with understanding, and with a glint of hope that after tonight Georgina could see he wouldn't do anything to hurt Milo.

"Yes, and no," she admitted. Jack scrunched his face with confusion, before she elaborated, "Yes, I look out for his well-being-and you don't exactly have the most stellar reputation, Jack-but it's more than that."

Jack's gaze locked with hers as he listened intently to what Georgina was saying. "I spent my whole life in fear of being rejected. Most of the men I've been with have either been married or not interested. Philip was boring, but he allowed me to have time to myself. He wouldn't even argue anything I asked of him. At first I thought it was great, but over time it became tedious and I began to see him as nothing more than a pawn who didn't challenge me. "

"And you wanted more, didn't you?" Jack finished, understanding sparkling his eyes.

Georgina nodded. "I've always been rejected. The ones that were married would never leave their wives for me. He was the only one who was there for me that could provide for Milo, but I've realized I want more. You feel like someone I could cling to and count on to be there for Milo."

Jack started to feel a glimmer of hope shining in his eyes, and her next words boosted his ego to new heights. "I want someone who makes me feel alive, someone who makes me feel like I'm living, instead of surviving. Someone like you, Jack. You've made me realize what it means to live in the moment. I like you, Jack, and I know you feel the same way about me."

Jacks lips curled up into a smile-not a smirk, a genuine smile he was sure he never sported a day in his life, and he felt elated. He didn't know what happiness felt like, but if it could make his heart race like this right now, his blood pulse, and his mind swirl with countless thoughts about what their future held then he never wanted to ignore this feeling a day in his life.

"I like you, Jack, and I don't want to lose you," she admitted in a barely audible voice, as if the words were painful to articulate. "I saw potential in us, and I didn't want to ruin it. But now I see I was just too afraid to give us a real chance, but I'm not going to run anymore."

"What are you saying, Sparks?" Jack asked as his face lit up with hope.

But she didn't articulate it in words, she spoke with her lips instead. Some things are said better in silent understanding. After all, some actions really did speak louder than words. She brought her body closer to his, closing the gap between them and her lips came closer to his, lingering for just a quick moment before they connected with Jack's.

Jack responded eagerly, surprised by her sudden action, but he didn't pull away. No, he liked the feel of her mouth in his, fighting for dominance, so he responded back, his tongue gliding against hers, sweeping, tasting, savoring the sweet taste of her.

Jack's kisses became more frantic and passionate, exploring her mouth more ardently as the passion started filling his senses. He was becoming aroused, and if he didn't stop himself, he wasn't sure how far this would go. He swept his tongue over hers in one final taste, savoring the feel of it, before pulling back.

"Georgina," he said, trying to search for his voice that was going to ruin this moment, he knew, but he couldn't do this with her right now. It took every fibre of his self control as a realization hit him like a ton of bricks: his nephew was right.

He didn't just want her for sex, he wanted so much more. A fact that shocked Jack to the core. He wanted to love her, to wake up next to her in the mornings, seeing Milo go off to school. He wanted to snuggle next to her, without having sex. He wanted to comfort her when she was having an off day, or conquer her enemies when they crossed her. He wanted this to be more than just a one-time, or two-time thing. He wanted a long-term relationship with her, something that shook him with utter surprise.

"Stop talking," Georgina complained, frustrated with Jack's futile attempts to ruin the moment, "and kiss me," she finished breathlessly.

"I can't," he responded, and Georgina looked up at him, not in anger, but in surprise. "You deserve better than this."

"Since when does the Jack Bass I know care about such things?" she pointed out. She knew the Basses, and thus Jack by association, her whole life, and from what she heard, Jack didn't care about another girl's feelings, he only cared about getting them into bed.

"Before you, never," he said in that 'what are you doing to me' voice. "But ever since that night, I can't stop thinking about you, and even more shockingly I want us to be together, not just for a night, I want us to be so much more."

Georgina raised her eyebrows. "The great Jack Bass, the master manipulator, wanting a real relationship, who would have ever thought?" she teased.

"Now you know," he responded back. I would rather we wait and get it right. How about we start with a date, say, in the next few days?"

Georgina was on cloud nine. She never thought Jack Bass of all people would ask her out on a date, but she supposed some people could surprise you, and she felt her smile sparkle with delight. "Okay, but Bass, it better not disappoint."

"I wouldn't dream of it," he said, returning her smile with the same gleam.

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Chuck felt drowsy after the day's festivities. He spent weeks preparing for the event to go off without a hitch, and much to his delight, it did. After the gala, Chuck was approached by the most senior member of Bass Industries board. Pete Holmberg. He made small talk with Chuck, before eventually moving onto business talk. To Chuck's delight, he was quite moved by Chuck's speech, saying his father would have been proud.

Chuck tried to not let that ruin his mood. Instead, he let a frosty smile light up his face. Chuck was still haunted by nightmares of Bart Bass-from his attempted murder to his constant displeasure and cruelty towards Chuck. He knew with certainty that if he and Blair ever had kids, he didn't want to resemble Bart as a parent in any way.

He wanted to lavish his children with love and devotion. He wanted them to know they were loved. Chuck and Blair hadn't exactly talked about their future, but one thing he did know was that he couldn't envision one without Blair. She was his rock; she held him together like glue.

When Chuck and Blair returned to their two story townhouse, Blair vacated to her bedroom to get into something more comfortable, while Chuck quickly removed his expensive suit and dress shirt. He removed his tie effortlessly, then plopped down in the lounge and picked up the newspaper, deciding to check the business section.

He was aware the headlines from today's gala wouldn't be out until sometime later in the week, but that didn't stop him from scanning the headlines. He spotted an article about Chuck's leadership at Bass Industries, calling his business tactics carefree and reckless.

Chuck scoffed at the headlines contents. If there was one thing Chuck was not these days, it was carefree, and he wasn't reckless with Blair loyally by his side. Chuck envisaged a future where he ruled Bass Industries with an iron fist, and, to do that, he needed to be ruthless in the business world. He needed to show step outside Bart's shadow and make changes.

He wanted to be more than Bart Bass's son and heir. He wanted people to respect him and see him as their fearless leader, one who had what it took to reign supreme as the company's top executive. Bart's mysterious death would have catastrophic consequences for his reputation. Most still believed Chuck pushed him off the rooftop, but those loyal to him knew the truth.

Just thinking about his late father was enough to send a chill up his spine.

Just as he became besieged by his own thoughts, his wife came towards him, dressed in her red silk nightgown that made her look sexy as hell. She curled up next to him, entwining their fingers together.

"What were you thinking about, Bass?" she inquired, concern glowing in her beautiful chocolate orbs.

"About us," he affirmed, but knowing he couldn't tell her a half truth. They were married now, and that, he knew, required honesty. "About my company, my father."

As Blair leaned into Chuck's chest, her fingers wandered up to his face, caressing it soothingly. "Chuck," she spoke with words of wisdom, "Your father can't hurt you if you don't let him; don't give him that power over you anymore," she inched closer to him, "And soon you'll have the Bass Board eating out of your hand. They'll see what a great leader you are."

Chuck listened to his wife's alleviating words, knowing she meant to diminish the pain his father's actions wrought upon him. But somehow they didn't soften the blow of his father's hatred towards him.

Blair began to stroke his face softly, leisurely moving down to his chest, were she began to rub circles around his chest, which started to lift Chuck's spirits.

He wanted so badly to forget the harm Bart caused him, as well as those he loved. He knew his wife was right, but somehow the nightmares of his father's attempted murder still ensnared him. His wife's advice gave him hope his father's grasp on him would wane over time.

Chuck soaked his wife's words, admiring her faith in him. She understood Chuck's relationship with his father better than anyone, and he loved her for it that much more. She saw something in him others deemed as weakness. She discovered his strength.

"How did the evening go? What happened between Jack and G? "she spoke as excitement flooded her eyes. "I never thought I would care, but for some reason I can't place, I do."

Chuck let a smirk curl his lips, taking in his wife's obvious enthusiasm. He agreed with his wife on that front: Jack and Georgina, in the past, were cruel and closed off. They thought their hearts were built with ice, but these past few days they had begun to see their frenemies in a different light.

Around each other, there seemed to be a light surrounding them, trying to find its way to beacon their hearts. They were different with each other, and it brought a smile to their faces. It was apparent they cared about one another. When Chuck witnessed Jack and Georgina's brief kiss, before they pulled apart and retired for the evening, Chuck saw how deeply their feelings went.

He looked their way, but was careful to remain hidden. Though he could barely make out their words, he did hear them faintly. Jack revealed to Georgina he cared about her for more than sex. It was a revelation Chuck knew was authentic. And for once in Chuck and Blair's lives, they were happy for them.

They wouldn't forget what Jack and Georgina had done to them, but just maybe they could build a new relationship with them, one that could earn them Chuck and Blair's complete trust over time, and provide them with allies. Jack and Georgina were proving themselves more and more.

Chuck's eyes glistened with earnest approval at his wife's words. He truly wanted his uncle's happiness. He knew how hollow it felt to be bombarded with solitude. It drove a person to do things they wouldn't wish upon anyone, and Chuck was pleased to see his uncle shine with happiness.

"Chuck," Blair sought Chuck's eyes, "Where do you see us in the future?"

Chuck paused, searching for an answer. He didn't know what their future entailed, other than never wanting to let her go. "I don't know that far into the future, but I do know I wouldn't dream of living it without you. I know we'll rule our empires, making them even more profitable then they are now."

Blair froze at his response. Did he just envision a life of work? Blair wanted many things, but she didn't want to become a workaholic like her mother. Just the thought had her reeling. She decided to press him further. "That's it? Just work? What about a family?"

Chuck's tone softened, "Of course I want a family with you one day, Blair. We need to be in a place where we're both ready for that first. I don't want to be plagued by memories of my father, because I don't want to be like him. I want to be better."

"And you will, Chuck," she assured. She knew Chuck held love and compassion in his heart, despite his past, and she continued to place her faith in him. "You have compassion and love for those you show your loyalty to. Bart was detached and cruel, something I know in my heart you could never be like when we have a family."

Chuck beamed at his wife's words. She placed her trust in him and he admired her for it. He loved her, and he never wanted to go a day without her. "I love you, Blair."

Blair smiled. "I love you too, Chuck." She kissed him, before she and Chuck drifted off into a peaceful, blissful sleep.

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The End

 ** _A/N: This is the end. I want to thank everyone for all the favorites, follows and reviews. I have more one-shot ideas that I want to write for this great couple. My next one will have to wait until I write another story for my other fandom. My next CB story will be an AU of 5x14 with Chuck helping Blair with Louis instead of Dan. It will most likely be posted under y another story. I'll try and update sooner than last time. But it probably won't be for a bit._**

 ** _Final thoughts? Please leave a review if you can, it encourages me to write more._**


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